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Identification
YMDB IDYMDB00313
NameCholesterol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholesterol is an extremely weak basic (essentially neutral) compound (based on its pKa). Cholesterol is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (-)-Cholesterol
  • (+)-ent-Cholesterol
  • (20bFH)-cholest-5-en-3b-ol
  • (3b)-cholest-5-en-3-ol
  • (3beta)-Cholest-5-en-3-ol
  • 20-epi-cholesterol
  • 20-iso-cholesterol
  • 20bFH-cholest-5-en-3b-ol
  • 3beta-Hydroxycholest-5-ene
  • 5-Cholesten-3B-ol
  • 5-Cholesten-3beta-ol
  • 5:6-Cholesten-3-ol
  • 5:6-Cholesten-3beta-ol
  • Cholest-5-en-3-ol
  • cholest-5-en-3b-ol
  • Cholest-5-en-3beta-ol
  • Cholesterin
  • Cholesterine
  • Cholesterol
  • Cholesterol base H
  • Cholesteryl alcohol
  • Cholestrin
  • Cholestrol
  • Cordulan
  • Dastar
  • Dusoline
  • Dusoran
  • Dythol
  • epicholesterin
  • Epicholesterol
  • Hydrocerin
  • Kathro
  • Lanol
  • Nimco cholesterol base H
  • Super hartolan
  • Tegolan
  • Fancol CH
  • Liquid crystal CN/9
  • nimco Cholesterol base no. 712
CAS number57-88-5
WeightAverage: 386.6535
Monoisotopic: 386.354866094
InChI KeyHVYWMOMLDIMFJA-FNOPAARDSA-N
InChIInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21?,22+,23-,24+,25+,26+,27-/m1/s1
IUPAC Name(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional IUPAC Namecholest-5-en-3-ol
Chemical FormulaC27H46O
SMILES[H]OC1([H])C([H])([H])C2=C([H])C([H])([H])[C@@]3([H])[C@]4([H])C([H])([H])C([H])([H])[C@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])[C@]3([H])[C@@]2(C([H])([H])[H])C([H])([H])C1([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Cholesterol
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting point148 °C
Experimental Properties
PropertyValueReference
Water Solubility9.5e-05 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.8e-05 g/LALOGPS
logP7.02ALOGPS
logP7.11ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.62 m³·mol⁻¹ChemAxon
Polarizability50.7 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Cholesterol biosynthesis and metabolism CE(10:0)PW002545 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(12:0)PW002548 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(14:0)PW002544 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(16:0)PW002550 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(18:0)PW002551 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Steroid biosynthesisec00100 Map00100
SMPDB Reactions
Desmosterol + NADPHCholesterol + NADP
7-Dehydrocholesterol + NADPHCholesterol + NADP
Cholesterol + Palmitic acidCE(18:0) + water
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-1109000000-3cc42021add80e72c319JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-3104900000-698223f49da0b0c1cf81JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-dccd68f70545aeac4fabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p9-3149000000-7f25daf2b709c7e0d177JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c00-6269000000-5333d0216e01a3e43367JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-dc853b29b9e884bbb03bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-09d9608700564a6fef78JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-1009000000-96f6e67651380e1c959eJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Zhu, Yongming; Qin, Liena; Liu, Rui. Simple method for synthesis cholesterol from Diosgenin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9 pp.
External Links:
ResourceLink
CHEBI ID16113
HMDB IDHMDB00067
Pubchem Compound ID5997
Kegg IDC00187
ChemSpider ID26000198
FOODB IDNot Available
WikipediaCholesterol
BioCyc IDCHOLESTEROL

Enzymes

General function:
Involved in O-acyltransferase activity
Specific function:
Ensures probably most of the acyltransferase activity. Suppression of ARE2 reduces sterol ester levels to 25% of the normal value
Gene Name:
ARE2
Uniprot ID:
P53629
Molecular weight:
74022.20313
Reactions
Acyl-CoA + cholesterol → CoA + cholesterol ester.
General function:
Involved in O-acyltransferase activity
Specific function:
Acyl-CoA + cholesterol = CoA + cholesterol ester
Gene Name:
ARE1
Uniprot ID:
P25628
Molecular weight:
71612.5
Reactions
Acyl-CoA + cholesterol → CoA + cholesterol ester.
General function:
Involved in lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism
Gene Name:
YEH2
Uniprot ID:
Q07950
Molecular weight:
62446.0
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.